Vat dyestuffs of the indigo series



' the further treatment is carriedrout as indiand dyes the ber from anoliVegreen vat i i g t Y C!!` v 'l 01j 2 V(e) l199.5 paas @fgac dimethyr-Chiom cated in Example 1, 4.7-4.7tetramethyl its properties, lthe .dyestufi obtained "in the abovev describedma'nner' is yery similarY tok that obtainable according to Example.v It Y dissolvesin 'sulfuric 'acid to a green solution ple l'. The dyestut has the following forf mula v n f 0 om om 2-'amino-1-ben`zo'ic acid ,of the melting point Y18S" C. to 190o C. are v boiled on'the reflux condenser with 120- parts 'ot Vmono-chloro- 'a'c`etic acid'and 200 part's'of sodium carb'onl ategin 5000 parts by volume of i'uzatery for about 6' hours ,until no`diazotizable substance A canv anyilonger'be detected. After-cooling,

' "the resulting 2.5'dimethylflichloro-phenylglycine-gfcarboxylic acid' is precipitated by Ineansfof hydrochloric acid, the mass fis iilf tered withsuct-ion, washed and dried.. KY26 parts of the lsaid; acid are heated with 150 parts oiaceticanhydride 'and 10 parts of anhydrous' sodiumacetate to boilinguntil'V` no nrtherrevolution Aof 'carboniclacidfis obs ervi'ed'.` The 'acetic anhydride is thendis- "billed in Vaqud'and'the residue is' washed /Wthwaten' f Y- fnThe resulting acetyl-indoxyl lderiyatiiie is 4 heated in 'an alkaline solutionfonthe steam bath and the 417-427tetramethyll'5f-di-- 'chlorindigo 'is'v obtained by lfblowingfair f y 5 v.-throughvthe'solutioni The-productjis'iiltered with suction, washed with Water and dried. It forms afblue powder. -The dyestu is p i l purified by'redissolving in. concentrated sulfuric acid.` Itis' identical with the dye- Y. L` g l c stuft obtained according to Example 2. .e

5(4) 156 partsof 4:-chlorl2L5Y-dimethyl-1- aniinobenzene are heated to boilingffor about 8 hours with-l20'parts of thevdiethyl ester of b'roino'.-Inalonic acid' in 1000 n partsA byA vol- 'urne of denatured alcohol.l After cooling the chloro phenyl camino malonic acid diethyl 'ester leftgkin'fthe filtrate inthe form of 'all "viscous oil.' lOOf'p'artsofrthis compound' are heated `in r,ound`botto'n1ed;iiask,*provided i withan inclined condenser to ateinperature 200 parts by Volume of a causticsodasolution tical with the. rdyestui v .toEXampleZ Y almost thesaine tintandmwithithe same fast-Y ness to washing and boiling and'chlorine as Vthe dyestuifobtaina'ble according to yExam-v 1 solvesin concentratedsulfuric acid't-a'fgreeh of 40Y1'l3e."and1500'parts volume of water,

y .the mass is boiled on a reflux condenser for 5,5dichlorindigo is obtained.' As regards about5 hours, and lthen the impurities con'` tained therein are iiltered ofi'.v By blowlng 5.151dif'zhlorindigol is obtained which'is idenobtainable according 8 4pY rts giycinegare V111mmrely @matrises-3o 'parts of powdered caustic sodaand 8 parts of sodiur'nami'de and ther mixturel is 'heated until f itv Inelts. When the evolution ot ammonia has The resulting' 4.427.71'tetrmethy1 indigo uis:

solution andl Vdyjes'the ber froman Jolivedyestuithus obtained `are introduced while stirring into SOOVparts'of anhydrous nitro- :.1- y green Vat grayish-bluetintsj 32 partsof the v benzene. To this suspension, jparts of broinline are slowly addedrdrop vby'drop, and" stirringis continued .for some tirneatroom v temperature and` massis finally. heated for' 6-'8 hours up toa temperature of'from 140? C' ttor '16.0 C, a l@thisitennlzerature the i l Vmass is stirred untilgrth'e evolution Qf hyd'rm g:

gen bromide has ceased-.s After. c'o'olin,f ,V the dyestuff is filtered-,with s uctionand freedV fromany adhering` solvent tbyhwashing it with alcohol.

- l As regardsy its properties/ the dyestu obtained in this manner, name-ff* Vly la7-4'3"-tetrainethyl-.5f-dibromindigo, is

identical with thatiobtained accordingv to Example 1.

We claim:

f 'LAS new"products; the dyestuffsiofthe fllwinggeneralzformulaf'f c green solution, yielding with an alkaline hy-Y drosfulite solution` volive-greenlv'a'ts from which bers aredyed'pure-blue tints ofgood fastness' to washing7 boiling? and chlorine.:-

ollowng formula' sais;

'2; `As a new praias@ the ayescn n .of @652129.

` vsoh'lton", yielding Wilth` an alkaline hydrO` I Ysulte solution an olive-green Vat from whchf 1 bersare ded pure-blue tints of good'fagst-` j ness ytolwams tures.

ing, boiling and chlorine. y In testimonyY whereof` we ax ou;` signa.I

Y KARL THIESS. v

REYNA.

Certificate of Correction Patent No. 1,792,130. v- Granted February 10, 1931, to y KARL THIESS n'r AL It is hereby certified that error appears in the printed specitcation of the abovenumbered patent requiring correction as follows: Page 1, lines 5 to 10, strike out the formula and insert instead Gili@l (Ima Hal \C=C/C Hal N/ \N l and that the said Letters Patent should beread with this correctiontherein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 24th day of March, A. D. 1931.

[SEAL] M. J. MOORE, Acting Commissioner of Patents. 

